This invention concerns phenoxypyridinyl ester insecticides and acaricides, intermediates for their preparation, agricultural compositions containing the insecticides and acaricides and their use to control pests.
U.S. Pat. No. 4,162,366 discloses the following alcohol for use in the preparation of insecticidal esters: ##STR1##
DE No. 2,810,881 discloses compounds of the following formula as insecticides: ##STR2## wherein X is independently C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, C.sub.1 to C.sub.4 alkylthio, C.sub.1 to C.sub.4 alkylsulfonyl, CF.sub.3, 3,4-methylenedioxy, Cl, F, or Br;
n is 0, 1 or 2; PA1 Y is O or S; PA1 R is H, CN, or C.tbd.CH; and PA1 Z is Cl, F or Br. PA1 X is H, CN, or C.tbd.CH; PA1 Y is H, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, C.sub.1 to C.sub.4 alkylthio, C.sub.1 to C.sub.4 alkylsulfonyl, CF.sub.3, 3,4-methylenedioxy, Cl, F or Br; PA1 n is 1 or 2; and PA1 Z is H, Cl or F. PA1 X is independently C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, C.sub.1 to C.sub.4 alkylthio, C.sub.1 to C.sub.4 alkylsulfinyl, C.sub.1 to C.sub.4 alkylsulfonyl, CF.sub.3, NO.sub.2, CN, Cl, F, Br, or 3,4-methylenedioxy; and PA1 R is H, CN, or C.tbd.CH. PA1 provided that Y and Z may be combined to form a perhalocyclopentylidene group; PA1 R is allethrolonyl, tetrahydrophthalimidomethyl, or R.sup.1 ; PA1 provided that R.sup.1 is other than phenoxybenzyl, .alpha.-cyanophenoxybenzyl, or .alpha.-ethylnylphenoxybenzyl; PA1 R.sup.2 is H, lower alkyl, ethynyl, CN, or trihalomethyl; PA1 R.sup.3 is divalent O, divalent S, or vinylene; and PA1 R.sup.4, R.sup.5, and R.sup.6 are independently H, lower alkyl, halogen, lower alkenyl, phenyl, phenoxy, benzyl, phenylthio, or any two joined to form a divalent methylenedioxy group; PA1 provided that when R.sup.4, R.sup.5 and R.sup.6 contains a phenyl ring, it may be substituted with one to three substituents selected from halogen or lower alkyl. PA1 R.sub.2 is H or halogen; PA1 R.sub.3 is H or halogen; PA1 R.sub.4 is H, Cl, Br, CN or optionally halo substituted alkyl; PA1 R.sub.5 is H, halogen or optionally halo substituted alkyl or alkoxy; PA1 R.sub.6 is isopropyl or cyclopropyl; and PA1 R.sub.7 is H, F, CF.sub.3, CHFCl or CF.sub.2 Cl. PA1 X.sub.1, X.sub.2, and X.sub.3, which may be the same or different each represent a hydrogen atom or a halogen atom, with the proviso that at least one represents a halogen atom; and B represents an alkyl radical of from 1 to 18 carbon atoms or a radical of the formula ##STR10## with the exception of compounds of the general formula in which X.sub.1, X.sub.2 and X.sub.3 each represents a fluorine. PA1 m is 0 or 1; PA1 R.sub.1 is H, C.sub.1 to C.sub.4 alkyl, C.sub.2 to C.sub.5 alkenyl, C.sub.2 to C.sub.5 alkynyl, C.sub.1 to C.sub.4 haloalkyl, C.sub.1 to C.sub.4 alkoxy, C.sub.1 to C.sub.4 haloalkoxy, C.sub.1 to C.sub.4 alkylthio, C.sub.1 to C.sub.4 alkylsulfinyl, C.sub.1 to C.sub.4 alkylsulfonyl, C.sub.1 to C.sub.4 haloalkylthio, C.sub.1 to C.sub.4 haloalkylsulfonyl, F, Cl, Br; when n=2, the R.sub.1 substituents, taken together, can be 3,4-methylenedioxy; PA1 R.sub.2 is H, F, Cl, Br, CH.sub.3, or CF.sub.3 ; PA1 R.sub.3 is F, Cl, Br, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 haloalkyl, CO.sub.2 CH.sub.3, or CO.sub.2 CH.sub.2 CH.sub.3 ; PA1 R.sub.4 is F, Cl, Br, or CH.sub.3 ; PA1 R.sub.5 is H, F, Cl, CF.sub.3, or C.sub.1 to C.sub.4 alkyl; PA1 R.sub.6 is Cl or Br; PA1 R.sub.7 is Cl or Br; PA1 R.sub.8 is H, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 haloalkyl, C.sub.1 to C.sub.4 alkoxy, C.sub.1 to C.sub.4 alkylthio, C.sub.1 to C.sub.4 alkylsulfinyl, C.sub.1 to C.sub.4 alkylsulfonyl, C.sub.1 to C.sub.4 haloalkylthio, C.sub.1 to C.sub.4 haloalkylsulfinyl, C.sub.1 to C.sub.4 haloalkylsulfonyl, F, Cl or Br; PA1 R.sub.9 is H, F, Cl, CH.sub.3, OCH.sub.3, or R.sub.8 and R.sub.9, taken together, can be 3,4-methylenedioxy; PA1 R.sub.10, R.sub.11, R.sub.12 and R.sub.13 are independently H, F, or Cl; and PA1 R.sub.14 is H, F, Cl, OCH.sub.3, OCH.sub.2 CH.sub.3, or C.sub.1 to C.sub.2 haloalkoxy. PA1 X is O; PA1 n is 1; PA1 m is 1; PA1 R.sub.1 is H, CH.sub.3, CF.sub.3, OCH.sub.3, OCF.sub.2 H, F, Cl, SCH.sub.3, SO.sub.2 CH.sub.3, SCF.sub.2 H, or SO.sub.2 CF.sub.2 H; PA1 R.sub.2 is H, F, or Cl; PA1 R.sub.8 is H, F, Cl, or C.sub.1 to C.sub.2 alkoxy; PA1 R.sub.9 is H; and PA1 R.sub.14 is H, F, Cl, OCH.sub.3, OCH.sub.2 CH.sub.3 or OCF.sub.2 H.
EP No. 145,661 discloses the following intermediates in the synthesis of insecticides: ##STR3## wherein X and Y are H, halo, NO.sub.2, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 haloalkyl, C.sub.1 to C.sub.4 alkoxy, C.sub.2 to C.sub.5 alkenyl, or C.sub.2 to C.sub.5 alkynyl.
AU No. 84/34,055 discloses compounds of the following formula as insecticides: ##STR4## wherein W is halogen;
U.S. Pat. No. 4,221,799 discloses compounds of the following formula as insecticides: ##STR5## wherein n is 0, 1, or 2;
U.S. Pat. No. 4,332,815 discloses compounds of the following formula as insecticides: ##STR6## wherein one of Y and Z is C.sub.1 to C.sub.4 perhaloalkyl and the other is H, halo, lower alkyl, phenyl, phenylthio, or benzyl;
European Patent Application No. 61,114 discloses esters of the following formula to be useful as insecticides: ##STR7## wherein: R is ##STR8## R.sub.1 is H, CN or optionally halo substituted C.sub.1 -C.sub.4 alkyl, alkenyl or alkynyl;
G.B. No. 2,108,123 discloses esters of the following formula to be useful as insecticides: ##STR9## wherein: Ar represents an optionally substituted aromatic or heteroaromatic radical;
Recent Advances In The Chemistry Of Insect Control, Janes (ed.), Royal Society of Chemistry, Burlington House, 1985, page 153, discloses a table of phenoxypyridyl esters of the formula: ##STR11## wherein: R.sub.1 is H, CN, CH.sub.3, CH.sub.2 CH.sub.3, ethynyl, ethenyl, CF.sub.3 or CH.sub.3 CO.sub.2 and R.sub.2 is phenyl or phenoxy.
U.S. Pat. No. 4,323,574 discloses compounds of the following formula as insecticides ##STR12## wherein: W is O or S.